Hackenberger Christian P R, O'Reilly Mary K, Imperiali Barbara
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
J Org Chem. 2005 Apr 29;70(9):3574-8. doi: 10.1021/jo047801v.
[reaction: see text] Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,beta-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.
[反应：见正文] 在此，我们将最近引入的在甲醇中使用氨基甲酸铵的方案应用于粗壳二糖的胺化反应，生成1,β-氨基壳二糖。与常用的基于碳酸氢铵的水溶性碳水化合物胺化反应相比，这个简单的一步法程序能够轻松制备不稳定的糖基胺。这种新的胺化方案改进了用于糖肽固相合成的关键壳二糖基-天冬酰胺构建块的合成。该方法的实用性通过合成一种39个氨基酸的糖蛋白得到了证明。
